FR3070162B1 - POLYESTERAMINES AND POLYESTERQUATS - Google Patents

Abstract

The present invention relates to compounds obtainable by the condensation by esterification of: A / an alkoxylated fatty amine of formula (I), or the product of partial or total quaternization of said alkoxylated fatty amine of formula (I): wherein R1 , AO, B, m, n, s and y are as defined in the description, B / with a dicarboxylic acid, or a derivative thereof, of formula (II): wherein D and R2 are as defined in the description, and C / with an (alkyl) alkanolamine derivative of formula (III) or the partial or total quaternization product of said (alkyl) alkanolamine derivative of formula (III): wherein R7, A''O, u and u 'are as defined in the description. The invention further relates to the use of said compound as surfactant, biocide, anticorrosion agent, wetting agent, and the like.

Description

POLYESTERAMINES AND POLYESTERQUATS

The present invention relates to compounds having polyesteramine and polyesterquat structures. Such structures are novel and compounds with such a structure can be used in many fields of application and, for example, as surfactants, as corrosion inhibitors and the like.

[0002] Fatty alkylamines and quaternary ammonium compounds are particularly useful chemicals used in a wide variety of industries. Among all possible applications, mention may be made of their use as biocides, hair care products, textile softeners or antistatic additives for plastics. Their strong adsorption properties on mineral or metallic surfaces or other solid particles, make them particularly interesting as wetting agents, corrosion inhibitors, ore beneficiation collectors, rock acid acid additive. phosphate, fertilizers and additives for surface treatment or internal treatment of mineral salts, anti-caking agents for hydrates, clay modifiers, lubricating additives or adhesion promoters. They can also have viscosifying, emulsifying or stabilizing properties useful for the oil and gas industry (demulsifying agents, surfactants for enhanced oil recovery, surfactants for fracture fluids, surfactants for acidifying fluids, surfactants for improving the flow of injectivity of produced water, surfactants for drilling muds), bitumen emulsion industry or detergency.

[0003] These fatty alkylamines and quaternary ammonium compounds are well known in the industry and research is ongoing to find new products. During the last 30 years, another family of compounds containing nitrogen of heavier molecular weight has been described in the literature. These compounds are amines and a quaternary ammonium with a polymeric or oligomeric structure. For example, patent EP0035263 describes a reaction product between a dicarboxylic acid and an ethoxylated fatty amine, said product being used as a textile softener. In EP0144975, the same reaction product can be quaternized and used as a hair conditioner.

The application W02008 / 089906 describes a reaction product of a fatty acid with a diacid and (alkyl) polyethanolamine, said reaction product is then quaternarized and used as a collector for the flotation of non-sulfide ores. Similarly, JP08-291281 discloses reaction products of C1-C22 alkylamines alkoxylated with diacids (or anhydrides) followed by quaternization reaction, said products being used as antistatic agent in composite resins, especially for the automotive industry.

[0007] WO 2011/147855 furthermore describes a reaction product of a fatty alcohol with a diacid and an (alkyl) polyethanolamine, optionally followed by a partial or total quaternization reaction, such a product being typically used for flotation. of silicates. The fatty alcohol may be replaced by an alkylated fatty amine having a single alkoxylated chain with a single terminating -OH function. Therefore, there is still a need for novel oligomeric compounds or cationic polymers for use in the fields of application listed above, said compound being more easily prepared, more stable, less expensive to synthesize and further having better environmental properties in terms of toxicity and biodegradability, and with improved technical performance.

Therefore, the present invention relates to a compound obtainable by the condensation by esterification of: A / an alkoxylated fatty amine of formula (I), or the partial or total quaternization product of said alkoxylated fatty amine of formula (I) I): in which:

R1 is selected from a hydrocarbyl group having 8 to 24 carbon atoms, preferably 10 to 24, more preferably 12 to 24 carbon atoms, and a group of the formula R4-O- (A'O) wT-, wherein R4 is a hydrocarbyl group having 8 to 24 carbon atoms, preferably 12 to 24 carbon atoms, w is an integer in the range of 0 to 20, preferably 0 to 10, more preferably 0 to 6, and more preferably from 0 to 4, ΑΌ is an alkyleneoxy group containing 2 to 4 carbon atoms, preferably 2 or 3 carbon atoms, more

preferably 2 carbon atoms; T is alkylene with 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, most preferably 2 or 3 carbon atoms, - AO is an alkyleneoxy group containing 2 to 4 carbon atoms, preferably 2 or 3 carbon atoms, more preferably 2 carbon atoms, - B is selected from C 1 -C 4 alkyl, aryl or arylalkyl group (e.g. phenyl, phenylalkyl, such as benzyl), m represents an integer from 1 to 20, preferably between 1 and 10, more preferably between 1 and 6, and even more preferably between 1 and 4 inclusive, n is an integer of 1 to 20, preferably 1 to 10, more preferably 1 to 10; and 6, and even more preferably between 1 and 4, inclusive, s is 1.2 or 3, preferably 2 or 3, and y is an integer of 0 to 5, preferably 0 to 3, more preferably y is 0 or 1, still more preferably y is 0, B / with a dicarboxylic acid , or a derivative thereof, of formula (II): in which

- D is selected from -F, -Cl, Br and -OR3, where R3 is hydrogen or a C1-C4 alkyl group, - R2 is selected from the group consisting of: o a direct bond, o a linear hydrocarbon chain or branched, saturated or unsaturated C1-C20 optionally substituted by one or more -OH groups, preferably an alkylene radical of the formula - (CH2) z-, wherein z is an integer of 1 to 20, preferably 1 to 10, preferably 2 to 6, and most preferably 4, a substituted alkylene radical, said alkylene radical being substituted with 1 or 2 -OH groups, an alkenylene radical having 1 to 20, preferably 1 at 10 carbon atoms, a substituted alkenylene radical,

said alkenylene radical being substituted with 1 or 2 methyl and / or methylene groups, o cycloalkylene, o cycloalkenylene and o arylene C / groups with an (alkyl) alkanolamine derivative of formula (III) or with the partial or total quaternization product of said (alkyl) alkanolamine derivative of formula (III): in which:

- O represents an alkyleneoxy group containing from 2 to 4 carbon atoms, preferably 2 or 3 carbon atoms, more preferably 2 carbon atoms, - u represents an integer between 1 and 20, preferably between 1 and 10 more preferably between 1 and 6, and still more preferably between 1 and 4, inclusive limits, u 'represents an integer of from 1 to 20, preferably from 1 to 10, more preferably from 1 to 6, and still more preferably between 1 and 4, inclusive, R 7 is selected from a hydrocarbyl group having 1 to 7, preferably 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms, an aryl or arylalkyl group (for example, a group phenyl or naphthyl), a group of the formula H- (OA-) V- (wherein v represents an integer of from 1 to 20, preferably from 1 to 10, more preferably from 1 to 6, and even more preferably from 1 to and 4, limits included), HO (CH2) q- and a group of e formula (IV)

wherein R8 and R9, which are identical or different, are selected from a hydrocarbyl group having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms and q is an integer of 1 to 10, preferably 2 to 6, limits included, and most preferably q is 2 or 3,

or R8 and R9 together with the nitrogen atom to which they are attached form a ring of 5, 6 or 7 atoms, optionally having one or more hetero atoms selected from oxygen, nitrogen, or sulfur.

In the present description, "hydrocarbyl" refers to a linear or branched hydrocarbyl chain, saturated or unsaturated.

In a preferred embodiment, compounds of the invention may be obtained by condensation by esterification as defined above, wherein, in the fatty amine of formula (I), R1 comprises 8, or more than 8, carbon atoms, typically 8 to 24 carbon atoms, preferably 10 to 24, more preferably 12 to 24 carbon atoms, inclusive, and in the (alkyl) alkanolamine derivative of formula (III) ), R7 has 6 or fewer carbon atoms, typically 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms, inclusive.

In a still more preferred embodiment, compounds of the invention may be obtained by condensation by esterification as defined above, in which, in the fatty amine of formula (I) and in the derivative of (alkyl) alkanolamine of formula (III), R1 and R7 are such that the difference in the number of carbon atoms they contain is greater than 2, typically from 2 to 23, preferably 5 to 23, more preferably at 23, limits included.

It is understood that the dicarboxylic acids or derivatives thereof of formula (II) further comprise their corresponding anhydride forms. It is further understood that when the alkyleneoxy chain contains more than one alkyleneoxy group, the alkyleneoxy groups may be the same or different. Similarly, when y is greater than one, the repeating patterns may be the same or different.

The present invention further relates to the compound of the present invention (obtainable by reaction between the alkoxylated fatty amine of formula (I), the dicarboxylic acid or a derivative thereof of formula (II), and the (alkyl) alkanolamine derivative of formula (III)), after further reaction wherein some or all of the nitrogen atoms are quaternized by reaction with a reagent of formula R5X, wherein R5 is selected from a hydrocarbyl group C 1 -C 6, preferably C 1 -C 4 alkyl, phenyl and phenylalkyl, such as benzyl, and X is any leaving group known in the art, and preferably X is generally selected from halogens, sulfates, and the like. , carbonates, and the like. The formula (1) below is a possible representation of the compounds of the present invention, as described above, obtainable by the condensation by esterification of the alkoxylated fatty amine of formula (I) (including its partial or total quaternization product), with the dicarboxylic acid, or a derivative thereof, of formula (II), and with an (alkyl) alkanolamine derivative of formula (III) (including its partial quaternization product or total).

Therefore, and in a second aspect, the present invention relates to a compound of general formula (1):

wherein: R2, R5 and X are as defined above, - t is 0 or 1 - p is an integer in the range of 1 to 15, preferably 1 to 10, more preferably 1 to 5, inclusive limits, - QO represents an alkyleneoxy group containing from 2 to 4 carbon atoms, preferably 2 or 3 carbon atoms, more preferably 2 carbon atoms, all the Q present in the compound of formula (1) can be identical or different, qi, q2, q3, q4, identical or different from each other, each represent an integer between 1 and 20, preferably between 1 and 10, more preferably between 1 and 6, and even more preferably between 1 and 4, limits inclusive, each R10, independently of the others, represents R7 as previously defined or a group R1- (G) y- in which R1 and y are as previously defined and G represents a group of formula (IV ):

in which B, R5, X, t and s are as defined above, the group (CH2) s is a spacer between the two nitrogen atoms to which it is bonded, given that at least one of the R10 groups represents R7, and at least one of R10 is R1- (G) y- and each t is independent of the others.

In a particular embodiment, the alkoxylated fatty amine of formula (I) is of formula (IA):

which is the alkoxylated fatty amine of formula (I) in which y represents 0, and R1, AO, m and n are as defined above, as well as its corresponding partially or totally quaternarized derivatives. In another particular embodiment, the (alkyl) alkanolamine derivative of formula (III) is of formula (IIIA):

which is the (alkyl) alkanolamine of formula (III) wherein u and u 'are each 1, A "O is ethylenoxy and R7 is as defined above In the compound of formula (IIIA) above, R7 is preferably a hydrocarbyl group having 1 to 4 carbon atoms The compound of formula (IIIA) above further covers its corresponding partially or fully quaternarized derivatives.

The derivative of dicarboxylic acid derivative of general formula (II) described may be a dicarboxylic acid or derivative of any dicarboxylic acid or anhydride known to those skilled in the art, and typically a dicarboxylic acid, a halide, for example a chloride, a dicarboxylic acid, a diester of a dicarboxylic acid, or a cyclic anhydride of a dicarboxylic acid. The most suitable derivatives are the dicarboxylic acids and their corresponding cyclic anhydrides.

Illustrative examples of dicarboxylic acid derivatives of the general formula (II) include oxalic acid, malonic acid, succinic acid, glutaric acid, glutaconic acid, adipic acid, lactic acid, and the like. muconic acid, pimelic acid, phthalic acid and its isomers, tetrahydrophthalic acid, malic acid, maleic acid, fumaric acid, suberic acid, mesaconic acid, acid sebacic acid, azelaic acid, tartaric acid, itaconic acid, glutinic acid, citraconic acid, brassylic acid, dodecanedioic acid, traumatic acid, thapsic acid, their corresponding acids, their corresponding methyl or ethyl esters, and their corresponding cyclic anhydrides, as well as mixtures thereof.

Preferred dicarboxylic acid derivatives of general formula (II) are selected from oxalic acid mentioned above, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, phthalic acid and its isomers, tetrahydrophthalic acid, malic acid, tartaric acid, itaconic acid, their corresponding acid chlorides, their corresponding methyl or ethyl esters, and their corresponding cyclic anhydrides, as well as mixtures thereof.

Alkoxylated fatty amines of formula (I) are available or may be prepared according to a process known in the literature, and may be, for example, easily prepared by alkoxylation of fatty amines of formula (a):

wherein R1, B, s and y are as defined above.

[0023] Illustrative examples of suitable fatty amines according to formula (a) for use as starting materials for the preparation of alkoxylated fatty amines of formula (I) include, but are not limited to, fatty amines of formula (a1) wherein y is 0 and fatty amines of formula (a2) wherein y is 1, s is 3 and B is methyl:

wherein R1 is as defined above.

Particular examples of amines of formula (a1) are amines of formula (a3): R4-O-T-NH2 (a3), wherein R4, and T are as defined above and w is 0.

More specific examples of the amines of formula (a) mentioned above include, but are not limited to, 2-ethylhexylamine, 2-propylheptylamine, n-octylamine, n-decylamine, n- dodecylamine, (coco-alkyl) amine, palm oil (alkyl) amine, n-tetradecylamine, n-hexadecylamine, n-octadecylamine, oleylamine, (tallow-alkyl) amine, tallow hydrogen-alkyl) amine, (colza-alkyl) amine, (soya-alkyl) amine, erucylamine, N- (n-decyl) -N-methyl-trimethylenediamine, N- (n-dodecyl) N-methyltrimethylenediamine, N- (cocoalkyl) -N-methyl-trimethylenediamine, N- (colza-alkyl) -N-methyl-trimethylenediamine, N (soya-alkyl) -N-methyl-trimethylenediamine, N- (tallow-alkyl) -N-methyl-trimethylenediamine, N- (hydrogenated tallow-alkyl) -N-methyl-trimethylenediamine, N-erucyl-N-methyltrimethylenediamine and isotridecyloxypropylamine, as well as mixtures of those -this.

According to one embodiment of the invention, the amines mentioned above are fatty amines obtained from oil or natural acids (plants or animals) and mixtures thereof, for example coconut fatty acids, tallow fatty acids, rapeseed oils, soybean oils and palm oils. These fatty amines are then typically alkoxylated with 2 to 40, preferably 2 to 20, more preferably 2 to 12 and even more preferably 2 to 8 EO (ethylene oxide units), and / or 2 to 40 preferably 2 to 20, more preferably 2 to 12 and still more preferably 2 to 8 PO (propylene oxide units), and / or 2 to 40, preferably 2 to 20, more preferably 2 to 12 and more preferably preferably 2 to 8 BO (butylene oxide units). Blocks with EO are generally added first and PO and / or BO last, or blocks with PO and / or BO added first and EO last, or with mixtures of EO and PO and / or BO to produce randomly alkoxylated products of the general formula (I). The alkoxylation can be carried out by any suitable method known in the art using, for example, an alkaline catalyst, such as potassium hydroxide (KOH), or an acid catalyst or even without catalyst.

Examples of products of formula (I) marketed include Noramox® SD20, Noramox® SD15, Noramox® S11, Noramox® S5, Noramox® S7, Noramox® S2, Noramox® SH2, Noramox® 02, Noramox® 05, Noramox® C2, Noramox® C5, Noramox® C15. All these marketed products are available from CECA S.A. Other examples of products of formula (I) marketed include Tomamine® E-17-5 and Tomamine® E-T-2, marketed by Air Products.

[0029] (Alkyl) alkanolamine derivatives of formula (III) are available or may be prepared according to a method described in the literature. Illustrative examples of suitable (alkyl) alkanolamine derivatives of formula (III) include, but are not limited to, triethanolamine, methyldiethanolamine, ethyldiethanolamine, propyldiethanolamine, butyldiethanolamine, isobutyldiethanolamine, pentyldiethanolamine, phenyldiethanolamine , hexyldiethanolamine, heptyldiethanolamine, and their corresponding alkoxylation products.

Other examples of suitable amines as starting material for the preparation of alkoxylated derivatives of formula (III) include, but are not limited to, methylamine, ethylamine, propylamines, butylamines, pentylamines, hexylamines, heptylamines, dimethylaminoethylamine, diethylaminoethylamine, dimethylaminopropylamine (DMAPA), diethylaminopropylamine (DEAPA), dipropylaminopropylamine, dibutylaminopropylamine (DBAPA), 1- (3-aminopropyl) -2-pyrolidine, 3-morpholinopropylamine, 1- (3-aminopropyl) piperidine, 1- (3-aminopropyl) pipecoline. Some of these alkoxylated derivatives of formula (III) are normal and, as such, form part of the present invention.

A suitable method for the preparation of products for use in the present invention comprises the steps of mixing at least one compound of formula (II) with at least one compound of formula (III) as defined above and at least one compound of formula (I) as defined above, and conducting a condensation reaction by esterification between the compounds in the mixture.

As will be apparent to those skilled in the art, other processes in which compounds of formula (I), (II) and (III) react sequentially with each other in different orders are also suitable. For example, it is possible to carry out an esterification condensation reaction between compounds of formula (I) and (II) in a first step, and then to carry out another condensation reaction by esterification of this condensation product with a compound of formula (III) in an additional step. Another suitable method comprises conducting a condensation reaction by esterification between compounds of formula (II) and (II) in a first step, and then conducting another condensation reaction by esterification of this condensation product with a compound of formula (I) in an additional step.

Other alternative methods include conducting a condensation reaction by esterification, such as for example, between: a. a condensation reaction product between compounds of formulas (II) and (III) and b. a condensation reaction product between compounds of formulas (I) and (II) c. optionally conducting another esterification reaction by esterification of the reaction product compounds of step a and step b above together with at least one compound of formula (I) and / or formula (II) and or formula (III).

More generally, the compounds of formula (1) of the present invention may be prepared from esterification condensation reaction (s) in which at least one compound of formula (I) and at least one compound of formula (I) II) and at least one compound of formula (III) react in one or more simultaneous esterification and / or sequential and / or alternating condensation reaction (s).

The esterification condensation reaction occurring between the compounds of formula (II) and of formula (I) and (III) is a reaction known per se in the art. The reaction is preferably carried out in the presence of an esterification catalyst, such as a Bronstedt acid or a Lewis acid, for example methanesulfonic acid, para-toluenesulfonic acid, hypophosphoric acid, citric acid. or boron trifluoride (BF3).

When a dicarboxylic acid derivative of formula (II), wherein D is O-R3, is used, the reaction is a transesterification which, alternatively, may be conducted in the presence of an alkaline catalyst. Alternatively, other conventional techniques known to those skilled in the art can be used from other derivatives of dicarboxylic acids, for example from their anhydrides or their acid chlorides.

As will be apparent to those skilled in the art, the various esterification reactions can be conducted with or without the addition of solvents. If solvents are present during the reaction, the solvents must be inert for esterification, for example, toluene or xylene, and the like.

The esterification condensation reaction between the components (I), (II) and (III) can be conducted at any temperature under known operating conditions and, for example, at a temperature typically in the range of 60 ° C at 300 ° C, preferably 120 ° C to 280 ° C, and generally for a time in the range of 1 hour to several hours, preferably 2 hours to 20 hours. The esterification condensation reaction may be conducted at atmospheric pressure, alternatively said reaction may optionally be conducted at a reduced pressure, for example from 500 Pa to 20000 Pa.

In a specific embodiment of the present invention, the molar ratio between the reagents [(I) + (III)] and (II) is 2: 1 to 1: 2, preferably 1.5: 1. at 1: 1.5, and most preferably 1.4: 1 to 1: 1.4.

According to another specific embodiment of the present invention, the molar ratio between the reagents [(I) + (III)] and (II) is from 2: 1 to 1: 1, preferably 2: 1 to 1.2: 1, and most preferably 2: 1 to 1.3: 1.

According to another additional embodiment, the molar ratio between (I) and (III) is from 15: 1 to 1:15, preferably from 10: 1 to 1:10, more preferably from 4: 1 to 1: 4, and most preferably 2: 1 to 1: 2.

When a quaternary product is desired, the preparation process may further comprise at least one step consisting of the addition of an alkylating agent to the reaction condensation product and the conduct of said quaternization reaction of the reaction product. condensation product, according to techniques known in the art. As such, when all t are 0 in formula (1), the product is a tertiary polyesteramine compound, and when all t are 1, the product is a quaternary polyester polyammonium compound, resulting in quaternarization of the compound wherein t is 0. As will be apparent to those skilled in the art, when part of the t are 0 and part of the t are 1, the product is a partially quaternized polyesteramine compound.

For the quaternization reaction step, the preferred alkylating agents are chosen from compounds of formula R5X. Illustrative examples of such alkylating agents include, but are not limited to, methyl chloride, methyl bromide, methyl iodide, dimethyl sulfate, diethyl sulfate, dimethyl carbonate, and chloride. benzyl, the most preferred alkylating agents being methyl chloride, dimethyl sulphate, diethyl sulphate or benzyl chloride and mixtures thereof, preferably methyl chloride and / or sulphate of dimethyl.

According to one variant, the quaternization can be carried out on the fatty amine of formula (I) and / or on the (alkyl) alkanolamine derivative of formula (III) before conducting the condensation reaction (s) by esterification with the dicarboxylic acid or a derivative thereof of formula (II). Other variants include the quaternarization reaction on the intermediate compounds obtained during sequential or alternating esterification condensation reactions. One or more total or partial quaternarization reaction (s) may be conducted after any of these intermediate steps.

The quaternization reactions are generally conducted in water and / or in one or more organic solvent (s), such as ethanol, isopropanol (IPA) or ethylene monobutyl ether. glycol, di (ethylene glycol) monobutyl ether (BDG), monoethylene glycol (MEG), diethylene glycol (DEG), or mixtures thereof. Preferred solvents are selected from isopropanol (IPA), ethanol, and mixtures thereof.

The quaternization reaction temperature is suitably in the range of 20 ° C to 100 ° C, preferably at least 40 ° C, more preferably at least 50 ° C and most preferably at least 55 ° C and preferably at most 90 ° C. The quaternization reaction is typically conducted for a time in the range of several tens of minutes to several tens of hours, preferably from one hour to 100 hours, more preferably from 1 hour to 30 hours. The quaternization reaction may be partial or total. Monitoring of the quaternarization reaction is generally performed by means of decreasing the total alkalinity of the reaction medium. "Total quaternization" is obtained when the total alkalinity value is less than or equal to 0.2 meq / g, preferably less than or equal to 0.1 meq / g, more preferably less than or equal to 0.05 meq / as measured by titration with hydrochloric acid.

In one embodiment, preferred compounds of formula (1) are those in which: R2 is selected from the group consisting of a divalent hydrocarbyl radical having from 1 to 10, preferably from 2 to 6, and from most preferably 4 carbon atoms, limits included, when R10 is R7, R7 is selected from a hydrocarbyl group having 1 to 4 carbon atoms, preferably 1 to 2 carbon atoms and most preferably R7 is methyl, when R10 is R1- (G) y-, y = 0 and R1 is selected from a hydrocarbyl group having 8 to 24 carbon atoms, preferably 12 to 24 carbon atoms, Q0 is ethoxy and p, q1, q2 , q3, q4, t, R5 are as defined above.

According to another embodiment, preferred compounds of formula (1) are those in which all "t" are equal to 1, that is to say that all the nitrogen atoms are quaternized (this which means a "total quarternisation"), all other groups and integer variables being as defined above.

According to another embodiment, preferred compounds of formula (1) are those in which all "t" are equal to 1, and R5 is selected from methyl and ethyl, all other groups and variable integers being such as defined above. According to another additional embodiment, preferred compounds of formula (1) are those in which all "t" are equal to 1, R5 is chosen from methyl and ethyl, and X is chosen from halogens and sulfates (eg, methosulfates), all other groups and variable integers being as defined above.

According to another embodiment, preferred compounds of formula (1) are those in which q1, q2, q3 and q4, independently of each other, are identical or different, and are chosen from 1,2,3 , 4, 5 and 6, p is in the range of 1 to 10 inclusive, and all other variable and integer groups are as defined above.

Particularly preferred compounds of formula (1) according to the present invention are those obtained by condensation reaction (s) by simultaneous (s) / sequential (s) / alternating esterification (s) of: at least one compound of formula (I), wherein y = 0, and R1 is selected from a hydrocarbyl group having 8 to 24 carbon atoms, preferably 10 to 24, more preferably 12 to 24 carbon atoms, at least one compound of formula (II) and at least one compound of formula (III) wherein R7 is a hydrocarbyl group having 1 to 7, preferably 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms, and their quaternarization reaction products partial or total.

The compounds of formula (1) most preferred according to the present invention are those obtained by condensation reaction (s) by simultaneous esterification (s) / sequential (s) / alternating (s) of: at least one compound of formula (I), wherein y = 0, R1 is selected from a hydrocarbyl group having 8 to 24 carbon atoms, preferably 10 to 24, more preferably 12 to 24 carbon atoms and AO is ethoxy, at least one formula (II), and at least one compound of formula (III), wherein R7 is a hydrocarbyl group having 1 to 7, preferably 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms, and A " is ethoxy, as well as their partial or total quaternarization reaction products.

Compounds of formula (1) which are particularly preferred in all according to the present invention are those obtained by reaction (s) of condensation by simultaneous (s) / sequential (s) / alternating esterification (s) of: at least one compound of formula (I), wherein y = 0, R1 is selected from a hydrocarbyl group having 8 to 24 carbon atoms, preferably 10 to 24, more preferably 12 to 24 carbon atoms, AO is ethoxy, and m and n , each independently of one another, identical or different, represent an integer between 1 to 10, preferably 1 to 6, more preferably 1 to 4 inclusive, at least one compound of formula (II), chosen of diacids (D is -OH) and their corresponding anhydrides, wherein R2 is a divalent hydrocarbyl radical having 1 to 14, more preferably 1 to 10, still more preferably 1 to 8 carbon atoms, inclusive, and at least one compound of formula (III), in R7 is a hydrocarbyl group having 1 to 7, preferably 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms, A "0 is ethoxy, and u and u 'are each 1, together with their reaction products total quaternization with methyl chloride.

Preferred compounds of formula (1) according to the present invention are those obtained by condensation reaction (s) by simultaneous esterification (s) / sequential (s) / alternating (s) of: at least one compound of formula (I) selected from n-octylamine, n-decylamine, n-dodecylamine, (coco-alkyl) amine, palm oil (alkyl palm) amine, n-tetradecylamine, n-hexadecylamine, n-d octadecylamine, oleylamine, (tallow-alkyl) amine, (hydrogenated tallow alkyl) amine, (rape-alkyl) amine, (soya-alkyl) amine, erucylamine, alkoxylated with 2 to 20, preferably 2 to 10 EO (ethylene oxide units), and / or 2 to 20, preferably 2 to 10 PO (propylene oxide units), at least one compound of formula (II) selected from 1 malonic acid, succinic acid, glutaric acid, glutaconic acid, adipic acid, muconic acid, pimelic acid, phthalic acid and its isomers, tetrahydrophthalic acid that malic acid, maleic acid, fumaric acid, suberic acid, mesaconic acid, sebacic acid, azelaic acid, tartaric acid, itaconic acid, glutinic acid, citraconic acid, brassylic acid, dodecanedioic acid, traumatic acid, thapsic acid, their corresponding acid chlorides, their corresponding methyl or ethyl esters, and their corresponding cyclic anhydrides, as well as mixtures thereof, and at least one compound of formula (III) selected from methyldiethanolamine, ethyldiethanolamine, propyldiethanolamine, butyldiethanolamine, isobutyldiethanolamine, pentyldiethanolamine, hexyldiethanolamine, heptyldiethanolamine, and their products. corresponding alkoxylation products, as well as their partial or total quaternarization reaction products.

More preferred compounds of formula (1) according to the present invention are those obtained by reaction (s) of simultaneous (s) / sequential (s) / alternating condensation (s) by esterification of: at least one compound of formula (I) selected from n-dodecylamine, (coco-alkyl) amine, palm oil-alkyl) amine, n-tetradecylamine, n-hexadecylamine, n-octadecylamine, oleylamine, tallow alkyl (amine), (hydrogenated tallow alkyl) amine, (rape-alkyl) amine, (soya-alkyl) amine, and erucylamine, alkoxylated with from 2 to 20, preferably from 2 to 10, EO (units of ethylene oxide), at least one compound of formula (II) selected from malonic acid, succinic acid, glutaric acid, glutaconic acid, adipic acid, muconic acid, acid pimelic acid, phthalic acid and its isomers, tetrahydrophthalic acid, malic acid, maleic acid, fumaric acid, suberic acid, mesaconic acid, sebacic acid, azelaic acid, tartaric acid, itaconic acid, glutinic acid, citraconic acid, brassylic acid, dodecanedioic acid, traumatic acid, thapsic acid, their chlorides of corresponding acids, their corresponding methyl or ethyl esters, and their corresponding cyclic anhydrides, as well as mixtures thereof, and at least one compound of formula (III) selected from methyldiethanolamine, ethyldiethanolamine, propyldiethanolamine, butyldiethanolamine, isobutyldiethanolamine, pentyldiethanolamine, hexyldiethanolamine, heptyldiethanolamine, as well as their corresponding ethoxylation products, as well as their partial or total quaternarization reaction products.

The compounds of formula (1) that are most preferred according to the present invention are those obtained by reaction (s) of condensation by simultaneous (s) / sequential (s) / alternating esterification (s) of: at least one compound of formula (I) selected from n-dodecylamine, (coco-alkyl) amine, palm oil (alkyl palm) amine, n-tetradecylamine, n-hexadecylamine, n-octadecylamine, oleylamine, tallow-alkyl) amine, (hydrogenated tallow alkyl) amine, (rape-alkyl) amine, (soya-alkyl) amine, erucylamine, alkoxylated with 2 to 20, preferably 2 to 10 ethylene oxide), at least one compound of formula (II) selected from malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, maleic acid, fumaric acid, suberic acid, sebacic acid, azelaic acid, brassylic acid, dodecanedioic acid, their corresponding cyclic anhydrides, and at least one compound of formula (III) selected from methyldiethanolamine, ethyldiethanolamine, propyldiethanolamine, butyldiethanolamine, isobutyldiethanolamine, pentyldiethanolamine, hexyldiethanolamine, heptyldiethanolamine, and their reaction products of total quaternization with methyl chloride .

The compounds of formula (1) according to the invention have many advantages, and among these advantages, it can be mentioned their preparation process which is relatively easy to implement, even on an industrial scale. Most of the compounds of formula (1) can be readily prepared from inexpensive and readily available starting materials.

The compound obtainable by the condensation by esterification of the alkoxylated fatty amine of formula (I) (comprising its partial or total quaternization product), with the dicarboxylic acid, or a derivative thereof, of formula (II), and with an (alkyl) alkanolamine derivative of formula (III) (comprising its partial or total quaternarization product), and more particularly the compound of formula (1), as defined above and according to The present invention has many interesting properties. As such, it may be used, by way of illustration only, and without limitation, as surfactant, biocide, anticorrosion agent, wetting agent, and the like.

As such, the compound obtainable by the condensation by esterification of the alkoxylated fatty amine of formula (I) (including its partial or total quaternization product), with the dicarboxylic acid, or a derivative of thereof, of formula (II), and with an (alkyl) alkanolamine derivative of formula (III) (comprising its partial or total quaternarization product), and more particularly the compound of formula (1) as defined above. it can be used in different applications among which may be mentioned uses as a collector for the enrichment (flotation) of ore, as a corrosion inhibitor, for example in the field of oil and gas production , as a viscosifier, emulsifier or stabilizer useful for the oil and gas industry (such as a demulsifier, surfactant to improve oil recovery, surfactant for fracturing fluids, surfactant for acidifying fluids, surfactant for improving the injectivity of produced water, surfactant for drilling muds, and the like), as a clay modifier, as an adhesion promoter, as an anti-caking additive, for example in the field of oil and gas production, as an additive in hair care products, as a fabric softener, as an antistatic agent in polymers , as a bitumen emulsion additive, as a cationic detergent agent, for example in the field of industrial detergency, car washing, as an additive for fertilizers, as an anti-caking agent for hydrates, as a lubrication additive or adhesion promoter, and the like.

The invention will become more clearly apparent from the following examples, which are presented by way of illustration only, without any intention to limit the scope of the protection sought as defined by the appended claims. Throughout the description, examples, and claims, all ranges of values are to be understood as "limits included" (ie, limits are included in those ranges), unless specifically indicated otherwise. .

Acid Index Measurement Method: In all of the following examples, the acid number is measured by potentiometric titration using a potassium hydroxide solution as the reagent and isopropyl alcohol as a reactant. than solvent.

In a beaker of 250 ml, about 10 g of sample to be analyzed are accurately weighed (Sw, accuracy per mg) and 70 ml of isopropyl alcohol are added. The mixture is stirred and gently heated, if necessary, to obtain a homogeneous sample. The combined reference glass electrode of the titrator is introduced into the solution, which is then stirred with a magnetic stirrer. The acid-base titration of the sample is performed using 0.1 N aqueous potassium hydroxide solution (KOH) and the change in pH is recorded on the titrator. The equivalent point is determined graphically using methods known to those skilled in the art, and the volume (VKOH, in ml) of potassium hydroxide solution used to reach this point is determined. The acid number (AV) is then obtained according to the following calculation:

Total Alkalinity Measurement Method: In all of the following examples, the total alkalinity value is measured by potentiometric titration using a hydrochloric acid solution as a reagent and isopropyl alcohol as the solvent.

In a polypropylene beaker of 100 ml, about 3 g of sample to be analyzed are accurately weighed (precision to mg, Sw to g) and 60 ml of isopropyl alcohol are added. The mixture is stirred and gently heated, if necessary, to obtain a homogeneous sample. Once the temperature of the solution has returned to room temperature, the combined reference glass electrode of the titrator is introduced into the solution, which is then stirred with a magnetic stirrer. The titration of the sample is carried out using a 0.2 N hydrochloric acid (HCl) solution of precisely known normality (N, in meq.ml'1). The evolution of the pH is recorded on the titrator. The equivalent point is determined using methods known to those skilled in the art, and the volume (VHCI, in ml) of hydrochloric acid solution used to reach this point is determined. The total alkalinity value (Alk) is then obtained according to the following calculation:

EXAMPLE 1: Synthesis of a Product A (According to the Invention) In a 4-liter round bottom flask, 1196.7 g (2.5 moles) of ethoxylated tallowamine (5OE) supplied by Arkema are introduced. under the trade name Noramox® S5, 715.2 g (3.45 moles) of methyldiethanolamine (> 99%) supplied by Taminco and 0.5 g of a 50% by weight aqueous hypophosphorous acid solution.

The mixture is heated to 80 ° C with nitrogen sparging. The bubbling is stopped and 756.8 g (5.18 moles) of adipic acid are then introduced with stirring. After 15 minutes, the temperature of the mixture is increased to 120 ° C over a period of 1 hour and the pressure in the tank is gradually decreased until a pressure of 6.66 kPa (50 mm Hg) be reached. The temperature is raised to 190 ° C and the temperature and pressure are maintained until substantially all the acid is consumed (acid number <5).

The system was then cooled to recover 2482.3 g of orange / brown crude liquid reaction product containing the desired esteramine, unreacted amines and unreacted diacid. EXAMPLE 2: Synthesis of a Product B (According to the Invention) In a 4-liter round bottom flask 1420.1 g (2.97 moles) of ethoxylated tallowamine (5OE) supplied by Arkema are introduced. under the trade name Noramox® S5, 353.2 g (2.97 moles) of methyldiethanolamine (> 99%) supplied by Taminco and 0.5 g of a 50% by weight aqueous hypophosphorous acid solution.

The mixture is heated at 80 ° C with nitrogen sparging. The bubbling is stopped and 650 g (4.45 mol) of adipic acid are then introduced with stirring. After 15 minutes, the temperature of the mixture is increased to 160 ° C and maintained for 4 hours. The temperature is then raised to 190 ° C and the temperature and pressure are maintained until substantially all the acid is consumed (acid number <5). The pressure in the tank is then gradually decreased until a pressure of 6.66 kPa (50 mmHg) is reached and the temperature and pressure are maintained for an additional 2 hours.

Finally, the system is cooled and the pressure is brought back to atmospheric pressure in order to recover 2260 g of orange / brown crude liquid reaction product containing the desired esteramine, unreacted amines and diacid. having not reacted. EXAMPLE 3 Synthesis of a Product C (According to the Invention) [0076] In a glass reactor of 61, 2022 g of the esteramine product A obtained in Example 1 are introduced with 453 g of isopropyl alcohol. Methyl chloride is added until the pressure in the tank reaches 290 kPa. The temperature is maintained at 80 ° C - 85 ° C until a complete reaction has occurred.

A total reaction is obtained when the total alkalinity value is less than or equal to 0.2 meq.g'1. The reactor is then allowed to cool to 65 ° C. and the pressure is brought back to atmospheric pressure. The mixture is sparged with nitrogen for 2 hours before 2095.9 g of the crude brown reaction product containing 6.7 wt.% Of isopropyl alcohol are recovered. EXAMPLE 4: Synthesis of a Product D (According to the Invention) In a glass reactor of 6 I, 1803.7 g of the esteramine product B obtained in Example 2 with 788.3 g are introduced. of isopropyl alcohol. Methyl chloride is added until the pressure in the tank reaches 290 kPa. The temperature is maintained at 80 ° C - 85 ° C until a complete reaction has occurred.

A total reaction is obtained when the total alkalinity value is less than or equal to 0.2 meq.g'1. The reactor is then allowed to cool to 65 ° C. and the pressure is brought back to atmospheric pressure. The mixture is sparged with nitrogen for 2 hours before recovering 2206.6 g of the crude brown reaction product still containing 17.3% by weight of isopropyl alcohol. EXAMPLE 5 Synthesis of a Product E (According to the Invention) [0080] In a dry autoclave of 4.55 g (5M) of MDEA (methyldiethanolamine) and 6 g of KOH (50% by weight aqueous solution) ) are added. The reactor is then closed and filled with a nitrogen atmosphere and the seal is protected against leakage. The MDEA and the catalyst are dehydrated to less than 1000 ppm water. The pressure is then increased to 75 kPa and 25 ° C with nitrogen. The temperature in the reactor is then increased to 90 ° C with stirring. Then, the temperature is again raised to 120 ° C and 40 g to 50 g of ethylene oxide are added. Additional ethylene oxide, for a total of 1100 g (25 M) in total, is added for 3 hours at 140 ° C - 150 ° C. After the addition of the ethylene oxide, the reaction mixture is maintained at this temperature for 30 minutes ("cooking"), then the liquid phase is subjected to nitrogen distillation. At the end of the reaction, the reactor is cooled to 60 ° C. and 1655 g of MDEA 5 EO are obtained.

In a 4-liter round-bottomed flask 1420.3 g (2.97 mol) of ethoxylated tallowamine (5OE) supplied by Arkema under the trade name Noramox® S5, 745.5 g (2%) are introduced. 97 moles) of MDEA 5OE (synthesized as described above) and 0.5 g of an aqueous solution of hypophosphorous acid at 50% by weight.

The mixture is heated to 80 ° C with nitrogen sparging. The bubbling is stopped and 650 g (4.45 mol) of adipic acid are then introduced with stirring. After 15 minutes, the temperature of the mixture is increased to 160 ° C and maintained for 4 hours. The temperature is then raised to 190 ° C and the temperature and pressure are maintained until substantially all the acid is consumed (acid number <5). The pressure in the tank is then gradually decreased until a pressure of 6.66 kPa (50 mmHg) is reached and the temperature and pressure are maintained for an additional 2 hours.

Finally, the system is cooled and the pressure is brought back to atmospheric pressure in order to recover 2654.5 g of orange / brown crude liquid reaction product containing the desired esteramine, the unreacted amines and the diacid not reacting. EXAMPLE 6 Synthesis of a Product F (According to the Invention) [0085] In a glass reactor of 61, 2050 g of the esteramine product E obtained in Example 5 are introduced with 615 g of isopropyl alcohol. Methyl chloride is added until the pressure in the tank reaches 290 kPa. The temperature is maintained at 80 ° C - 85 ° C until a complete reaction has occurred.

A total reaction is obtained when the total alkalinity value is less than or equal to 0.2 meq.g'1. The reactor is then allowed to cool to 65 ° C. and the pressure is brought back to atmospheric pressure. The mixture is sparged with nitrogen for 2 hours before 2496.9 g of the crude brown reaction product containing 12.4% by weight of isopropyl alcohol is recovered. EXAMPLE 7 Synthesis of a Product G (According to the Invention)

In a dry autoclave 41, 510 g (5 M) of DMAPA (dimethylaminopropylamine) and 5 g (1% by weight) of water are added. The reactor is then closed and filled with a nitrogen atmosphere and the seal is protected against leakage. The pressure is then increased to 100 kPa and 30 ° C with nitrogen. The temperature in the reactor is then increased to 120 ° C with stirring. 40 g of ethylene oxide are added. The temperature is increased linearly until the reaction begins. Additional ethylene oxide, for a total of 1100 g (25 M) in total, is added for 4 hours at 150 ° C - 160 ° C. After the addition of the ethylene oxide, the reaction mixture is maintained at this temperature for 30 minutes ("cooking"), then the liquid phase is subjected to nitrogen distillation. At the end of the reaction, the reactor is cooled to 60 ° C. and 1570 g of DMAPA 5 EO are obtained.

1196.1 g (2.5 moles) of ethoxylated tallowamine (5OE) supplied by Arkema under the trade name Noramox® S5, 805.4 g (2%), are introduced into a 4-liter round-bottomed flask. 5 moles) of DMAPA 5OE (synthesized as described above) and 0.5 g of a 50% by weight aqueous hypophosphorous acid solution.

The mixture is heated to 80 ° C with nitrogen sparging. The bubbling is stopped and 547.9 g (3.75 moles) of adipic acid are then introduced with stirring. After 15 minutes, the temperature of the mixture is increased to 160 ° C and maintained for 4 hours. The temperature is then raised to 190 ° C and the temperature and pressure are maintained until substantially all the acid is consumed (acid number <5). The pressure in the tank is then gradually decreased until a pressure of 6.66 kPa (50 mmHg) is reached and the temperature and pressure are maintained for an additional 2 hours.

Finally, the system is cooled and the pressure is brought back to atmospheric pressure in order to recover 2413.9 g of orange / brown crude liquid reaction product containing the desired esteramine, the unreacted amines and the diacid not reacting. EXAMPLE 8 Synthesis of a Product H (According to the Invention) [0091] In a glass reactor of 61, 2040 g of the esteramine product E obtained in Example 5 are introduced with 600 g of isopropyl alcohol. Methyl chloride is added until the pressure in the tank reaches 290 kPa. The temperature is maintained at 80 ° C - 85 ° C until a complete reaction has occurred.

A total reaction is obtained when the total alkalinity value is less than or equal to 0.2 meq.g'1. The reactor is then allowed to cool to 65 ° C. and the pressure is brought back to atmospheric pressure. The mixture is sparged with nitrogen for 2 hours before 2396.7 g of the crude brown reaction product containing 12.9% by weight of isopropyl alcohol are recovered. EXAMPLE 9 Synthesis of Products I to R According to the Invention According to the same process as in Example 1, the following products were prepared from the compounds indicated in Table 1 below:

TABLE 1 Compounds and Quantities Used to Synthesize Products I to R According to the Invention

NoxS5 is an ethoxylated tallow amine (5OE) supplied by Arkema under the trade name Noramox® S5

NoxS2 is an ethoxylated tallow amine (2OE) supplied by Arkema under the trade name Noramox® S2

NoxS11 is an ethoxylated tallow amine (11OE) supplied by Arkema under the trade name Noramox® S11

NoxC5 is an ethoxylated cocoamine (5OE) supplied by Arkema under the trade name Noramox® C5 MDEA is methyldiethanolamine (> 99%) supplied by Taminco TEA is triethanolamine (> 99%) supplied by Taminco MDEA is methyldiethanolamine (> 99%) provided by Taminco MDEA 5 OE is as described in Example 5

Ac. Ad. Denotes adipic acid, Anh. Suck, refers to succinic anhydride and Anh. Male. refers to maleic anhydride. EXAMPLE 10 Synthesis of Products S to AB (According to the Invention) According to the same process as in Example 3, the quaternary chloromethylammonium derivatives of products I to R were prepared from the compounds indicated in Table 2 below:

TABLE 2 Compounds and Quantities Used to Synthesize Products S to AB According to the Invention

Claims (17)

1. Composed! obtained by the esterification condensation of: A / an alkoxylated fatty amine of formula (I), or the product of partial or total quaternization of said alkoxylated fatty amine of formula (I): in which: R1 is selected from a hydrocarbyl group having 8 to 24 carbon atoms, preferably 10 to 24, more preferably 12 to 24 carbon atoms, and a group of the formula R4-O- (A'O) wT-, wherein R4 is a hydrocarbyl group having 8 to 24 carbon atoms, preferably 12 to 24 carbon atoms, w is an integer in the range of 0 to 20, preferably 0 to 10, more preferably 0 to 6, and more preferably from 0 to 4, ΑΌ is an alkyleneoxy group containing 2 to 4 carbon atoms, preferably 2 or 3 carbon atoms, more preferably 2 carbon atoms; T is alkylene with 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, most preferably 2 or 3 carbon atoms, - AO is an alkyleneoxy group containing 2 to 4 carbon atoms, preferably 2 or 3 carbon atoms, more preferably 2 carbon atoms, - B is selected from C 1 -C 4 alkyl, aryl or arylalkyl (e.g. phenyl, phenylalkyl, such as benzyl), m is an integer of from 1 to 20 carbon atoms; preferably between 1 and 10, more preferably between 1 and 6, and even more preferably between 1 and 4, inclusive limits, - n represents an integer of from 1 to 20, preferably from 1 to 10, more preferably from 1 to 10; 6, and even more preferably between 1 and 4 inclusive, - s is 1, 2 or 3, preferably 2 or 3, and - y is an integer of 0 to 5, preferably 0 to 3, more preferably y is 0 or 1, still more preferably y is 0, B / with a dicarboxylic acid, or a derivative thereof, of formula (II): in which - D is selected from -F, -Cl, Br and -OR3, where R3 is hydrogen or a C1-C4 alkyl group, - R2 is selected from the group consisting of: o a direct bond, o a linear hydrocarbon chain or branched, saturated or unsaturated C1-C20 optionally substituted by one or more -OH groups, preferably an alkylene radical of the formula - (CH2) z-, wherein z is an integer of 1 to 20, preferably 1 to 10, preferably 2 to 6, and most preferably 4, a substituted alkylene radical, said alkylene radical being substituted with 1 or 2 -OH groups, an alkenylene radical having 1 to 20, preferably 1 to 10 carbon atoms, a substituted alkenylene radical, said alkenylene radical being substituted with 1 or 2 methyl and / or methylene groups, o cycloalkylene, o cycloalkenylene and o arylene C / with an (alkyl) alkanolamine derivative of the formula (III) or the product of partial quaternisation or of said (alkyl) alkanolamine derivative of formula (III): - O represents an alkyleneoxy group containing from 2 to 4 carbon atoms, preferably 2 or 3 carbon atoms, more preferably 2 carbon atoms, - u represents an integer between 1 and 20, preferably between 1 and 10 , more preferably between 1 and 6, and even more preferably between 1 and 4, limits included, u 'represents an integer between 1 and 20, preferably between 1 and 10, more preferably between 1 and 6, and even more preferably between 1 and 4, inclusive limits, - R 3 * * * 7 is selected from a hydrocarbyl group having 1 to 7, preferably 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms, aryl or arylalkyl (e.g., phenyl or naphthyl), a group of the formula H- (OA-) - (wherein v represents an integer from 1 to 20, preferably from 1 to 10, more preferably from 1 to 6, and even more preferably from 1 to 4 inclusive), HO (CH 2) q- and a group of formula (IV) wherein R8 and R9, identical or different, are selected from a hydrocarbyl group having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms and q is an integer of 1 to 10, preferably 2 to 6, limiting inclusive, and most preferably q is 2 or 3, or R 8 and R 9, together with the nitrogen atom to which they are attached form a ring of 5, 6 or 7 atoms, optionally having one or more hetero atoms (s). ) selected from oxygen, nitrogen or sulfur. 2. Compound according to claim 1, wherein the radical R1 of the fatty amine of formula (I) has from 8 to 24 carbon atoms, preferably from 10 to 24, more preferably from 12 to 24 carbon atoms, limits inclusive, and the R7 radical of the (alkyl) alkanolamine derivative of formula (III) has 6 or less carbon atoms, typically 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms, inclusive. 3. A compound according to claim 1 or claim 2, wherein the radical R1 and the radical R7 of the fatty amine of formula (I) and the (alkyl) alkanolamine derivative of formula (III) respectively, are such that the the difference in the number of carbon atoms they contain is greater than 2, typically from 2 to 23, preferably from 5 to 23, more preferably from 10 to 23 inclusive. A compound according to any one of claims 1 to 3, wherein a part or all of the nitrogen atoms further react with a reagent of formula R5X, wherein R5 is selected from a C1-C6 hydrocarbyl group, preferably C 1 -C 4 alkyl, phenyl and phenylalkyl, such as benzyl, and X is selected from halogens, sulfates, carbonates. 5. Compound according to any one of claims 1 to 4, wherein the alkoxylated fatty amine of formula (I) is of formula (IA): which is the alkoxylated fatty amine of formula (I) wherein y represents 0, and R1, AO, m and n are as defined in claim 1, as well as its corresponding partially or fully quaternarized derivatives. 6. A compound according to any one of claims 1 to 5, wherein the (alkyl) alkanolamine derivative of formula (III) is of formula (IIIA): which is the (alkyl) alkanolamine of formula (III) wherein u and u 'are each 1, A "O is ethylenoxy and R7 is as defined in claim 1, and is preferably a hydrocarbyl group having 1 to 4 carbon atoms, as well as its corresponding partially or fully quaternarized derivatives. A compound according to any of claims 1 to 6, wherein the (alkyl) alkanolamine derivatives of formula (III) include triethanolamine, methyldiethanolamine, ethyldiethanolamine, propyldiethanolamine, butyldiethanolamine, isobutyldiethanolamine, pentyldiethanolamine, phenyldiethanolamine, hexyldiethanolamine, heptyldiethanolamine, and their corresponding alkoxylation products. 8. A compound according to any one of claims 1 to 7, wherein the dicarboxylic acid derivative of general formula (II) is selected from a dicarboxylic acid, a dicarboxylic acid halide, a diester of a dicarboxylic acid, or a cyclic anhydride of a dicarboxylic acid. A compound according to any one of claims 1 to 8, wherein the dicarboxylic acid derivatives of the general formula (II) include oxalic acid, malonic acid, succinic acid, glutaric acid, glutaconic acid, adipic acid, muconic acid, pimelic acid, phthalic acid and its isomers, tetrahydrophthalic acid, malic acid, maleic acid; fumaric acid, suberic acid, mesaconic acid, sebacic acid, azelaic acid, tartaric acid, itaconic acid, glutinic acid, citraconic acid, brassylic acid, dodecanedioic acid, traumatic acid, thapsic acid, their corresponding acid chlorides, their corresponding methyl or ethyl esters, and their corresponding cyclic anhydrides, as well as mixtures thereof. A compound according to any one of claims 1 to 9, wherein the molar ratio between the reagents [(I) + (III)] and (II) is 2: 1 to 1: 2, preferably 1.5 : 1 to 1: 1.5, and most preferably 1.4: 1 to 1: 1.4. The compound according to any one of claims 1 to 9, wherein the molar ratio between the reagents [(I) + (III)] and (II) is 2: 1 to 1: 1, preferably 2: 1. at 1.2: 1, and most preferably 2: 1 to 1.3: 1. The compound of any one of claims 1 to 11, wherein the molar ratio of (I) to (III) is from 15: 1 to 1:15, preferably 10: 1 to 1:10, more preferably 4 : 1 to 1: 4, and most preferably 2: 1 to 1: 2. 13. Compound of general formula (1): wherein: R2 is selected from the group consisting of: o a direct bond, o a linear or branched, saturated or unsaturated C1-C20 hydrocarbon chain optionally substituted by one or more -OH group (s), preferably an alkylene group of formula - (CH2) Z-, wherein z is an integer of 1 to 20, preferably 1 to 10, preferably 2 to 6, and most preferably 4, a substituted alkylene radical, said radical alkylene being substituted with 1 or 2 -OH groups, an alkenylene radical having 1 to 20, preferably 1 to 10 carbon atoms, a substituted alkenylene radical, said alkenylene radical being substituted with 1 or 2 methyl groups and / or methylene a cycloalkylene, cycloalkenylene and arylene group R5 is selected from a C1-C6 hydrocarbyl group, preferably a C1-C4 alkyl, phenyl and phenylalkyl group, such as benzyl. X is selected from halogens, sulfates, carbonates, t is 0 or 1 p is an integer in the range of 1 to 15, preferably 1 to 10, more preferably 1 to 5, inclusive, QO is one alkyleneoxy group containing from 2 to 4 carbon atoms, preferably 2 or 3 carbon atoms, more preferably 2 carbon atoms, knowing that all Q present in the compound of formula (1) may be identical or different, qi, q2 , q3, q4, identical or different from each other, each represent an integer between 1 and 20, preferably between 1 and 10, more preferably between 1 and 6, and even more preferably between 1 and 4, inclusive limits, each R10 group, independently of the others, represents R7 or a group R1- (G) y-, R7 is selected from a hydrocarbyl group having 1 to 7, preferably 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms aryl or arylalkyl (e.g., phenyl or naphthyl), a group of the formula H- (OA-) v- (wherein v is an integer of 1 to 20, preferably 1 to 10, plus preferably between 1 and 6, and even more preferably between 1 and 4 inclusive), HO (CH 2) q - and a group of formula (IV) wherein R8 and R9, identical or different, are selected from a hydrocarbyl group having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms and q is an integer of 1 to 10, preferably 2 to 6, limiting inclusive, and most preferably q is 2 or 3, or R 8 and R 9, together with the nitrogen atom to which they are attached form a ring of 5, 6 or 7 atoms, optionally having one or more hetero atoms (s). ) selected from oxygen, nitrogen or sulfur. R1 is selected from a hydrocarbyl group having 8 to 24 carbon atoms, preferably 10 to 24, more preferably 12 to 24 carbon atoms, and a group of the formula R4-O- (A'O) wT-, wherein R4 is a hydrocarbyl group having 8 to 24 carbon atoms, preferably 12 to 24 carbon atoms, w is an integer in the range of 0 to 20, preferably 0 to 10, more preferably 0 to 6, and more preferably preferably from 0 to 4, ΑΌ is an alkyleneoxy group containing 2 to 4 carbon atoms, preferably 2 or 3 carbon atoms, more preferably 2 carbon atoms; T is alkylene with 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, most preferably 2 or 3 carbon atoms, y is an integer of 0 to 5, preferably 0 to 3, more preferably y is 0 or 1, still more preferably y is 0, and G is a group of formula (IV): wherein R5, X and t are as defined above, - B is selected from C1-C4 alkyl, aryl or arylalkyl (e.g. phenyl, phenylalkyl, such as benzyl), and - s is 1, 2 or 3, preferably 2 or 3, wherein at least one of R 10 is R 7, and at least one of R 10 is R 1 - (G) y - and each t is independent of the others. The compound of claim 13, wherein: R2 is selected from the group consisting of a divalent hydrocarbyl radical having from 1 to 10, preferably from 2 to 6, and most preferably 4 carbon atoms, inclusive when R10 is R7, R7 is selected from a hydrocarbyl group having 1 to 4 carbon atoms, preferably 1 to 2 carbon atoms and most preferably R7 is methyl, when R10 is R1- (G) y-, y = 0 and R1 is selected from a hydrocarbyl group having 8 to 24 carbon atoms, preferably 12 to 24 carbon atoms, Q0 is ethoxy and p, q1, q2, q3, q4, t, R5 and X are as defined in claim 13. The compound of claim 13 or claim 14, wherein all "t" are 1. 16. A compound according to any one of claims 13 to 15 being obtained from the condensation reaction (s) by simultaneous esterification (s) / sequential (s) / alternating (s) of: at least one compound of formula (I), wherein y = 0, and R1 is selected from a hydrocarbyl group having 8 to 24 carbon atoms, preferably 10 to 24, more preferably 12 to 24 carbon atoms, at least one compound of formula ( II), and at least one compound of formula (III), wherein R7 is a hydrocarbyl group having 1 to 7, preferably 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms, and their partial quaternization reaction products or total. 17. Use of a compound according to any one of claims 1 to 16 as a collector for the enrichment (flotation) of ore, as a corrosion inhibitor, as viscosifier, emulsifier or stabilizer useful for l oil and gas industry, as a clay modifier, as an adhesion promoter, as an anti-caking additive, as an additive in hair care products, as a fabric softener as an antistatic agent in polymers, as a bitumen emulsion additive, as a cationic detergent agent, as an additive for fertilizers, as an anti-caking agent for hydrates, as a lubrication additive or adhesion promoter.